Organic letters

Cycloaddition Reactions of Thiazolium Azomethine Ylides: Application to Pyrrolo [2, 1-b] thiazoles

CR Berry, CA Zificsak, AC Gibbs, DJ Hlasta

Index: Berry, Craig R.; Zificsak, Craig A.; Gibbs, Alan C.; Hlasta, Dennis J. Organic Letters, 2007 , vol. 9, # 21 p. 4099 - 4102

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Citation Number: 13

Abstract

Thiazolium azomethine ylides, equipped with a C-2 methanethiol group, participate in an efficient [3+ 2] cycloaddition reaction with acetylene derivatives to yield unique pyrrolo [2, 1- b] thiazoles. The elimination of the methanethiol leaving group from the cycloadduct has replaced the need for a separate oxidation step and suppresses ring-opening side reactions. Products were obtained in short synthetic sequences to demonstrate their use ...

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